#------------------------------------------------------------------------------ #$Date: 2023-11-16 01:37:55 +0200 (Thu, 16 Nov 2023) $ #$Revision: 287627 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247737.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7247737 loop_ _publ_author_name 'Baraboshkin, Nikita' 'Zelenov, Victor Petrovich' 'Fedyanin, Ivan V.' _publ_section_title ; What are the prospects of [1,2,5]oxadiazolo[3,4-c]cinnoline 5-oxides, 1,5-dioxides and their nitro derivatives as high-energy-density materials? Synthesis, experimental and predicted crystal structures, and calculated explosive properties ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D3CE00964E _journal_year 2023 _chemical_absolute_configuration unk _chemical_formula_moiety 'C8 H3 N5 O5' _chemical_formula_sum 'C8 H3 N5 O5' _chemical_formula_weight 249.15 _space_group_crystal_system orthorhombic _space_group_IT_number 33 _space_group_name_Hall 'P 2c -2n' _space_group_name_H-M_alt 'P n a 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2023-01-30 _audit_creation_method ; Olex2 1.5 (compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429) ; _audit_update_record ; 2023-08-15 deposited with the CCDC. 2023-11-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.40027(12) _cell_length_b 10.46252(9) _cell_length_c 6.13809(5) _cell_measurement_reflns_used 9515 _cell_measurement_temperature 99.98(15) _cell_measurement_theta_max 77.0910 _cell_measurement_theta_min 5.2140 _cell_volume 924.784(13) _computing_cell_refinement 'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)' _computing_data_collection 'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)' _computing_data_reduction 'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 99.98(15) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -111.00 -14.00 0.50 0.36 -- -86.25 83.00 31.00 194 2 \w -44.00 -14.00 0.50 0.36 -- -86.25 39.00-117.00 60 3 \w -44.00 23.00 0.50 0.09 -- -48.70 39.00-117.00 134 4 \w 68.00 94.00 0.50 0.36 -- 107.75-153.00-136.00 52 5 \w 82.00 107.00 0.50 0.36 -- 107.75-125.00-120.00 50 6 \w 39.00 72.00 0.50 0.36 -- 107.75-108.00-105.53 66 7 \w 39.00 72.00 0.50 0.36 -- 107.75-125.00-120.00 66 8 \w 82.00 107.00 0.50 0.36 -- 107.75 -83.00 -89.00 50 9 \w 79.00 104.00 0.50 0.36 -- 107.75-108.00-105.53 50 10 \w 46.00 89.00 0.50 0.36 -- 107.75-125.00 0.00 86 11 \w 50.00 75.00 0.50 0.36 -- 107.75-121.00 23.00 50 12 \w 56.00 103.00 0.50 0.36 -- 107.75-107.00 169.67 94 13 \w -23.00 44.00 0.50 0.09 -- 48.70 -39.00 88.00 134 14 \w 43.00 76.00 0.50 0.36 -- 107.75 -77.00 120.00 66 15 \w 42.00 89.00 0.50 0.36 -- 107.75 -77.00 30.00 94 16 \w 45.00 83.00 0.50 0.36 -- 107.75 -69.00 176.30 76 17 \w 38.00 91.00 0.50 0.36 -- 107.75 -77.00 0.00 106 18 \w 49.00 82.00 0.50 0.36 -- 107.75 -77.00 -30.00 66 19 \w 43.00 71.00 0.50 0.36 -- 107.75 -61.00 30.00 56 20 \w 37.00 63.00 0.50 0.36 -- 107.75 -61.00 90.00 52 21 \w 36.00 69.00 0.50 0.36 -- 107.75 -61.00 -30.00 66 22 \w 36.00 70.00 0.50 0.36 -- 107.75 -61.00 -60.00 68 23 \w 36.00 61.00 0.50 0.36 -- 107.75 -61.00-120.00 50 24 \w 45.00 71.00 0.50 0.36 -- 107.75 -77.00-180.00 52 25 \w 38.00 71.00 0.50 0.36 -- 107.75 -61.00 60.00 66 26 \w 127.00 153.00 0.50 0.36 -- 107.75 30.00 0.00 52 27 \w 100.00 133.00 0.50 0.36 -- 107.75 45.00 -60.00 66 28 \w 97.00 178.00 0.50 0.36 -- 107.75 39.00-117.00 162 29 \w 153.00 178.00 0.50 0.36 -- 107.75 45.00 -60.00 50 30 \w 107.00 153.00 0.50 0.36 -- 107.75 45.00 30.00 92 31 \w 97.00 122.00 0.50 0.36 -- 107.75 30.00 150.00 50 32 \w 130.00 178.00 0.50 0.36 -- 107.75 30.00 150.00 96 33 \w 117.00 155.00 0.50 0.36 -- 107.75 83.00 31.00 76 34 \w 137.00 163.00 0.50 0.36 -- 107.75 125.00 -60.00 52 35 \w 76.00 158.00 0.50 0.36 -- 107.75 153.00 -94.00 164 36 \w 99.00 125.00 0.50 0.36 -- 107.75 125.00 -60.00 52 37 \w 124.00 149.00 0.50 0.36 -- 107.75 121.00 105.00 50 38 \w -158.00 -75.00 0.50 0.36 -- -86.25 -39.00 88.00 166 39 \w -121.00 -39.00 0.50 0.09 -- -48.70 -39.00 88.00 164 40 \w -158.00 -79.00 0.50 0.36 -- -86.25 -83.00 -89.00 158 41 \w -120.00 -54.00 0.50 0.09 -- -48.70-153.00-136.00 132 42 \w -146.00 -54.00 0.50 0.36 -- -86.25-153.00-136.00 184 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0456779000 _diffrn_orient_matrix_UB_12 0.1128969000 _diffrn_orient_matrix_UB_13 -0.1201207000 _diffrn_orient_matrix_UB_21 0.0960193000 _diffrn_orient_matrix_UB_22 -0.0624762000 _diffrn_orient_matrix_UB_23 0.0305903000 _diffrn_orient_matrix_UB_31 -0.0117275000 _diffrn_orient_matrix_UB_32 -0.0709415000 _diffrn_orient_matrix_UB_33 -0.2182532000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0466 _diffrn_reflns_av_unetI/netI 0.0255 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 11803 _diffrn_reflns_point_group_measured_fraction_full 0.871 _diffrn_reflns_point_group_measured_fraction_max 0.869 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 77.688 _diffrn_reflns_theta_min 5.226 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.344 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.72010 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.790 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 504 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.194 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.049 _refine_ls_abs_structure_details ; Flack x determined using 625 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.24(14) _refine_ls_extinction_coef 0.0069(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 164 _refine_ls_number_reflns 1716 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.077 _refine_ls_R_factor_all 0.0310 _refine_ls_R_factor_gt 0.0308 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0584P)^2^+0.1363P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0830 _refine_ls_wR_factor_ref 0.0831 _reflns_Friedel_coverage 0.586 _reflns_Friedel_fraction_full 0.714 _reflns_Friedel_fraction_max 0.711 _reflns_number_gt 1703 _reflns_number_total 1716 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00964e2.cif _cod_data_source_block z456301 _cod_original_cell_volume 924.783(13) _cod_database_code 7247737 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula C8H3N5O5 _chemical_oxdiff_usercomment Z456301 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C2(H2), C4(H4), C5(H5) ; _shelx_res_file ; TITL Z456301.res in Pna2(1) z456301.res created by SHELXL-2018/3 at 22:53:50 on 30-Jan-2023 REM Old TITL 23NDI_R009 in Pna2(1) REM SHELXT solution in Pna2(1) REM R1 0.070, Rweak 0.023, Alpha 0.005, Orientation as input REM Flack x = 0.311 ( 0.123 ) from Parsons' quotients REM Formula found by SHELXT: C13 N O4 CELL 1.54184 14.400266 10.462524 6.138086 90 90 90 ZERR 4 0.000124 0.00009 0.000049 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,+Z SYMM 0.5-X,0.5+Y,0.5+Z SFAC C H N O UNIT 32 12 20 20 L.S. 4 PLAN 5 TEMP -173 CONF BOND $H list 4 HTAB fmap 2 53 acta MORE -1 REM REM REM WGHT 0.058400 0.136300 EXTI 0.006933 FVAR 1.04040 O1 4 0.180015 0.351914 0.369342 11.00000 0.02441 0.01917 = 0.02268 0.00404 -0.00209 -0.00438 N1 3 0.425667 0.550419 0.828307 11.00000 0.01777 0.01944 = 0.01703 0.00077 0.00006 0.00398 C1 1 0.381041 0.583336 0.623212 11.00000 0.01715 0.01811 = 0.01528 0.00011 -0.00014 0.00465 O2 4 0.175684 0.464619 0.072344 11.00000 0.02519 0.02311 = 0.01900 0.00168 -0.00636 -0.00102 N2 3 0.493510 0.614448 0.916278 11.00000 0.01870 0.02488 = 0.01972 -0.00231 -0.00397 0.00467 C2 1 0.311458 0.502394 0.547709 11.00000 0.01677 0.01701 = 0.01680 0.00104 0.00189 0.00243 AFIX 43 H2 2 0.292258 0.429472 0.628181 11.00000 -1.20000 AFIX 0 N3 3 0.596803 0.784915 0.855179 11.00000 0.02207 0.02913 = 0.02797 -0.00258 -0.00413 0.00070 O3 4 0.395406 0.454234 0.927022 11.00000 0.02483 0.02231 = 0.02003 0.00501 -0.00066 0.00289 C3 1 0.271886 0.533267 0.350759 11.00000 0.01597 0.01550 = 0.01729 -0.00086 0.00101 0.00128 O4 4 0.607202 0.875843 0.695186 11.00000 0.02067 0.03013 = 0.02941 -0.00382 -0.00462 -0.00618 N4 3 0.534134 0.857237 0.529860 11.00000 0.01749 0.02351 = 0.02263 -0.00308 0.00025 -0.00230 C4 1 0.294685 0.642417 0.231139 11.00000 0.02045 0.01796 = 0.01659 0.00127 0.00087 0.00145 AFIX 43 H4 2 0.263125 0.661938 0.099363 11.00000 -1.20000 AFIX 0 N5 3 0.203864 0.443804 0.257165 11.00000 0.01607 0.01589 = 0.01925 0.00052 -0.00092 0.00194 O5 4 0.533353 0.928217 0.372067 11.00000 0.02857 0.02976 = 0.02843 0.00419 0.00259 -0.00945 C5 1 0.364187 0.721430 0.308693 11.00000 0.02081 0.01647 = 0.01810 0.00084 0.00144 0.00098 AFIX 43 H5 2 0.381380 0.795912 0.229892 11.00000 -1.20000 AFIX 0 C6 1 0.408986 0.690874 0.504024 11.00000 0.01575 0.01747 = 0.01725 -0.00144 0.00280 0.00164 C7 1 0.485211 0.758175 0.598563 11.00000 0.01685 0.01797 = 0.02107 -0.00337 0.00165 0.00090 C8 1 0.524383 0.717115 0.795843 11.00000 0.01705 0.02089 = 0.02123 -0.00421 0.00008 0.00308 HKLF 4 REM Z456301.res in Pna2(1) REM wR2 = 0.083129, GooF = S = 1.07699, Restrained GooF = 1.07664 for all data REM R1 = 0.030811 for 1703 Fo > 4sig(Fo) and 0.030966 for all 1716 data REM 164 parameters refined using 1 restraints END WGHT 0.0583 0.1386 REM Instructions for potential hydrogen bonds EQIV $1 -x+1/2, y+1/2, z-1/2 HTAB C4 O1_$1 REM Highest difference peak 0.194, deepest hole -0.203, 1-sigma level 0.049 Q1 1 0.4536 0.7371 0.5425 11.00000 0.05 0.19 Q2 1 0.3968 0.6335 0.8281 11.00000 0.05 0.18 Q3 1 0.6045 0.9773 0.6955 11.00000 0.05 0.17 Q4 1 0.5799 0.8967 0.8765 11.00000 0.05 0.17 Q5 1 0.6492 0.8628 0.9019 11.00000 0.05 0.17 ; _shelx_res_checksum 3383 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.406 _oxdiff_exptl_absorpt_empirical_full_min 0.361 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.18002(10) 0.35191(13) 0.3693(3) 0.0221(3) Uani 1 1 d . . . . . N1 N 0.42567(10) 0.55042(15) 0.8283(3) 0.0181(4) Uani 1 1 d . . . . . C1 C 0.38104(13) 0.58334(18) 0.6232(3) 0.0168(4) Uani 1 1 d . . . . . O2 O 0.17568(10) 0.46462(13) 0.0723(3) 0.0224(4) Uani 1 1 d . . . . . N2 N 0.49351(12) 0.61445(16) 0.9163(3) 0.0211(4) Uani 1 1 d . . . . . C2 C 0.31146(12) 0.50239(18) 0.5477(4) 0.0169(4) Uani 1 1 d . . . . . H2 H 0.292258 0.429472 0.628181 0.020 Uiso 1 1 calc R U . . . N3 N 0.59680(12) 0.78491(17) 0.8552(4) 0.0264(4) Uani 1 1 d . . . . . O3 O 0.39541(10) 0.45423(13) 0.9270(3) 0.0224(4) Uani 1 1 d . . . . . C3 C 0.27189(12) 0.53327(16) 0.3508(4) 0.0163(4) Uani 1 1 d . . . . . O4 O 0.60720(10) 0.87584(14) 0.6952(3) 0.0267(4) Uani 1 1 d . . . . . N4 N 0.53413(11) 0.85724(16) 0.5299(3) 0.0212(4) Uani 1 1 d . . . . . C4 C 0.29469(13) 0.64242(17) 0.2311(4) 0.0183(4) Uani 1 1 d . . . . . H4 H 0.263125 0.661938 0.099363 0.022 Uiso 1 1 calc R U . . . N5 N 0.20386(11) 0.44380(15) 0.2572(3) 0.0171(4) Uani 1 1 d . . . . . O5 O 0.53335(10) 0.92822(15) 0.3721(3) 0.0289(4) Uani 1 1 d . . . . . C5 C 0.36419(13) 0.72143(18) 0.3087(3) 0.0185(4) Uani 1 1 d . . . . . H5 H 0.381380 0.795912 0.229892 0.022 Uiso 1 1 calc R U . . . C6 C 0.40899(13) 0.69087(18) 0.5040(4) 0.0168(4) Uani 1 1 d . . . . . C7 C 0.48521(13) 0.75818(18) 0.5986(4) 0.0186(4) Uani 1 1 d . . . . . C8 C 0.52438(13) 0.71711(18) 0.7958(4) 0.0197(4) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0244(7) 0.0192(6) 0.0227(8) 0.0040(6) -0.0021(6) -0.0044(5) N1 0.0178(7) 0.0194(7) 0.0170(9) 0.0008(6) 0.0001(7) 0.0040(6) C1 0.0172(8) 0.0181(8) 0.0153(11) 0.0001(7) -0.0001(8) 0.0046(6) O2 0.0252(7) 0.0231(7) 0.0190(8) 0.0017(6) -0.0064(6) -0.0010(5) N2 0.0187(7) 0.0249(8) 0.0197(10) -0.0023(7) -0.0040(7) 0.0047(6) C2 0.0168(8) 0.0170(8) 0.0168(11) 0.0010(7) 0.0019(7) 0.0024(6) N3 0.0221(8) 0.0291(9) 0.0280(11) -0.0026(8) -0.0041(8) 0.0007(6) O3 0.0248(7) 0.0223(7) 0.0200(8) 0.0050(6) -0.0007(6) 0.0029(5) C3 0.0160(7) 0.0155(8) 0.0173(10) -0.0009(8) 0.0010(8) 0.0013(6) O4 0.0207(6) 0.0301(7) 0.0294(10) -0.0038(7) -0.0046(7) -0.0062(6) N4 0.0175(7) 0.0235(8) 0.0226(11) -0.0031(7) 0.0003(7) -0.0023(6) C4 0.0205(8) 0.0180(8) 0.0166(10) 0.0013(8) 0.0009(8) 0.0014(6) N5 0.0161(7) 0.0159(7) 0.0193(9) 0.0005(7) -0.0009(7) 0.0019(5) O5 0.0286(7) 0.0298(7) 0.0284(10) 0.0042(7) 0.0026(7) -0.0095(6) C5 0.0208(8) 0.0165(8) 0.0181(11) 0.0008(7) 0.0014(8) 0.0010(6) C6 0.0158(7) 0.0175(8) 0.0173(10) -0.0014(7) 0.0028(8) 0.0016(6) C7 0.0168(8) 0.0180(8) 0.0211(12) -0.0034(8) 0.0016(8) 0.0009(6) C8 0.0171(8) 0.0209(9) 0.0212(12) -0.0042(8) 0.0001(8) 0.0031(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C1 124.65(17) . . ? O3 N1 C1 117.07(16) . . ? O3 N1 N2 118.28(18) . . ? C2 C1 N1 117.53(17) . . ? C2 C1 C6 121.45(18) . . ? C6 C1 N1 121.00(17) . . ? N1 N2 C8 114.89(18) . . ? C1 C2 H2 121.7 . . ? C3 C2 C1 116.64(18) . . ? C3 C2 H2 121.7 . . ? C8 N3 O4 105.20(19) . . ? C2 C3 C4 123.84(18) . . ? C2 C3 N5 118.01(16) . . ? C4 C3 N5 118.12(18) . . ? N3 O4 N4 108.80(14) . . ? O5 N4 O4 118.18(16) . . ? O5 N4 C7 136.48(19) . . ? C7 N4 O4 105.32(17) . . ? C3 C4 H4 120.7 . . ? C5 C4 C3 118.6(2) . . ? C5 C4 H4 120.7 . . ? O1 N5 C3 117.64(17) . . ? O2 N5 O1 124.37(17) . . ? O2 N5 C3 117.98(17) . . ? C4 C5 H5 120.3 . . ? C4 C5 C6 119.50(18) . . ? C6 C5 H5 120.3 . . ? C1 C6 C7 113.87(18) . . ? C5 C6 C1 119.92(18) . . ? C5 C6 C7 126.19(18) . . ? N4 C7 C6 131.8(2) . . ? N4 C7 C8 107.52(18) . . ? C8 C7 C6 120.59(18) . . ? N2 C8 C7 124.89(18) . . ? N3 C8 N2 121.9(2) . . ? N3 C8 C7 113.2(2) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N5 1.231(2) . ? N1 C1 1.455(3) . ? N1 N2 1.302(3) . ? N1 O3 1.253(2) . ? C1 C2 1.391(3) . ? C1 C6 1.401(3) . ? O2 N5 1.224(3) . ? N2 C8 1.378(3) . ? C2 H2 0.9500 . ? C2 C3 1.375(3) . ? N3 O4 1.375(3) . ? N3 C8 1.313(3) . ? C3 C4 1.397(3) . ? C3 N5 1.472(2) . ? O4 N4 1.475(2) . ? N4 O5 1.221(3) . ? N4 C7 1.322(3) . ? C4 H4 0.9500 . ? C4 C5 1.383(3) . ? C5 H5 0.9500 . ? C5 C6 1.399(3) . ? C6 C7 1.427(3) . ? C7 C8 1.403(3) . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -178.30(16) . . . . ? N1 C1 C6 C5 -179.18(16) . . . . ? N1 C1 C6 C7 2.3(2) . . . . ? N1 N2 C8 N3 -174.78(18) . . . . ? N1 N2 C8 C7 3.4(3) . . . . ? C1 N1 N2 C8 -2.2(3) . . . . ? C1 C2 C3 C4 -3.0(3) . . . . ? C1 C2 C3 N5 174.83(16) . . . . ? C1 C6 C7 N4 175.2(2) . . . . ? C1 C6 C7 C8 -1.3(2) . . . . ? N2 N1 C1 C2 177.86(17) . . . . ? N2 N1 C1 C6 -0.6(3) . . . . ? C2 C1 C6 C5 2.5(3) . . . . ? C2 C1 C6 C7 -176.08(17) . . . . ? C2 C3 C4 C5 3.3(3) . . . . ? C2 C3 N5 O1 6.3(2) . . . . ? C2 C3 N5 O2 -172.77(16) . . . . ? N3 O4 N4 O5 -178.67(18) . . . . ? N3 O4 N4 C7 -0.1(2) . . . . ? O3 N1 C1 C2 -3.0(2) . . . . ? O3 N1 C1 C6 178.63(16) . . . . ? O3 N1 N2 C8 178.58(16) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? O4 N3 C8 N2 178.87(17) . . . . ? O4 N3 C8 C7 0.5(2) . . . . ? O4 N4 C7 C6 -176.43(18) . . . . ? O4 N4 C7 C8 0.4(2) . . . . ? N4 C7 C8 N2 -178.90(18) . . . . ? N4 C7 C8 N3 -0.6(2) . . . . ? C4 C3 N5 O1 -175.73(17) . . . . ? C4 C3 N5 O2 5.2(3) . . . . ? C4 C5 C6 C1 -2.2(3) . . . . ? C4 C5 C6 C7 176.12(18) . . . . ? N5 C3 C4 C5 -174.59(16) . . . . ? O5 N4 C7 C6 1.7(4) . . . . ? O5 N4 C7 C8 178.6(2) . . . . ? C5 C6 C7 N4 -3.2(3) . . . . ? C5 C6 C7 C8 -179.69(18) . . . . ? C6 C1 C2 C3 0.1(3) . . . . ? C6 C7 C8 N2 -1.6(3) . . . . ? C6 C7 C8 N3 176.64(18) . . . . ? C8 N3 O4 N4 -0.3(2) . . . . ?